Hikes and Historic Homes Go Hand-in-hand in This Gorgeous Corner of New England

Bartholomew's Cobble
Photo: Courtesy of R.Cheek

If you’ve never sniffed the mountain air — or heard the door of a centuries-old Colonial home creak — in the Berkshires, then you are, without a doubt, missing out on something magical. This western region of Massachusetts abounds with historic charm and wholesome outdoor activities, and there’s one land conservation organization that offers both by the bundle.

The Trustees, short for the Trustees of Reservations, conserves more than 100 properties, from tracts of land to historical homes, across Massachusetts. Founded in 1891 by landscape architect Charles Eliot, the nonprofit also offers endless opportunities for exploration. To me, it lies at the intersection of adventure and architecture, hikes and houses. Nowhere is this more true than at the Trustees’ properties in Western Mass. From heart-pumping trails to stunning design, the place has all the trappings of a classically New England autumn adventure.

The Hikes

Monument Mountain

Kick off a Berkshires trip with a stunning journey up Monument Mountain. A hike to its 1,640-foot summit, called Squaw Peak, rewards you with sweeping views of the Housatonic River Valley and the southern Berkshires. Below the summit, a white quartzite overlook called the Devil’s Pulpit frames views of the Taconic Range in New York. They’re the same views that authors Nathaniel Hawthorne and Herman Melville saw when discussing their most recent works: "The Scarlet Letter"and "Moby Dick." What’s a New England hike without a little literary cred?

Monument Mountain Reservation, Route 7, Great Barrington, Mass., trustees.org.

Monument Mountain
Courtesy of R.Cheek

Bartholomew’s Cobble

Strolling through Bartholomew’s Cobble feels like jumping into the pages of the storybook. It’s a landscape so idyllic, you’ll wonder why you left your picnic basket behind. The place was created when the Taconic and Berkshire ranges formed some 500 million years ago. Circle the cobble’s rocky outcroppings first, then head through meadow’s tractor path to Hulburt’s Hill for panoramas of the surrounding fields.

Bartholomew’s Cobble, 105 Weatogue Rd., Ashley Falls, Sheffield, Mass., trustees.org.

Goose Pond Reservation

This forested reservation is home to part of the Appalachian Trail. Situated in the town of Lee, a hike here rises 300 feet to a rocky ridge, where you can see the sparkling waters of a mountainside lake called Lower Goose Pond. Step between moss-covered rocks along this two-mile trail for an afternoon well spent.

Ridge St., Lee, Mass., trustees.org.

Mountain Meadow Preserve

Expect wildflowers of all scents and hues at Mountain Meadow Preserve. Up near the border of Vermont, this scenic spot lays out four miles of trails for meandering. A nature-filled walk starts by crossing a meadow, then ascends a hilltop that offers views of the valley below and nearby Mount Greylock.

Mason Street, Williamstown, Mass., trustees.org.

The Historic Homes

Naumkeag East Facade
Courtesy of Trustees


Naumkeag is one of the grandest “cottages” in Western Massachusetts. Built in 1887 by the Choate family, the Gilded Age estate in Stockbridge is filled with unexpected details. The Shingle-style main house flaunts 44 rooms with intricate woodwork and stunning antiques, while outside, one-of-a-kind gardens and terraces overlook views of the Berkshire hills.

5 Prospect Hill Rd., Stockbridge, Mass., thetrustees.org.

Courtesy of Ogden Gigli

The Mission House

Step inside the Mission House to glimpse an impressive collection of 18th-century American furniture and art — and to learn the history of Native Americans who lived in the area. Originally built in 1742 on a hill in Stockbridge, the house was later moved to its current location on Main Street in the 1930s. The building housed the first missionary to the Mohican tribe, Rev. John Sergeant. Today, you can wind through the gardens in the backyard to visit a small Native American museum.

19 Main Street, Stockbridge, Mass., trustees.org.

Ashley House
Courtesy of Trustees

Ashley House

The Ashley House is one of the oldest houses in the southern swath of the Berkshires. Built in 1735 by Colonel John Ashley, the center-chimney Colonial harbors a whole lot of history. Over the years, its owner amassed some 3,000 acres of land (including what’s currently Bartholomew’s Cobble) and wealth, thanks in part to five enslaved people on the property. One of them, named Elizabeth Freemen, helped put an end to slavery in Massachusetts by suing Col. Ashley for her freedom and winning.

117 Cooper Hill Road, Ashley Falls, Sheffield, Mass., trustees.org.

Field Farm
Courtesy of Trustees

Field Farm

Most of the historic house museums in the Berkshires date back centuries, but the Folly at Field Farm is a mere 54 years old. Still, it’s rich in architectural history. Designed by Ulrich Franzen, the Folly’s curving walls and floor-to-ceiling windows take cues from International-style design. Inside, custom furniture and accents establish a midcentury modern vibe, while outside, four miles of trails crisscross the property and pass by 13 whimsical sculptures.

554 Sloan Rd., Williamstown, Mass., thetrustees.org.

Where to Stay

Guest House at Field Farm
Courtesy of Madeline Bilis

For a southern Berkshires jaunt, book a cozy room at the ever-quaint Red Lion Inn. An iconic presence on Stockbridge's Main Street, the inn is one of only a few hotels in America that has been in business prior to 1800. (On your visit, head to the cellar for a pint at the Lion’s Den, where there’s live music every night.) Further north in Williamstown, check into the Guest House at Field Farm. The farm’s other International-style building has stunning contemporary artworks and mountain views, not to mention a seasonal pool and a terrace.

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